Azodyestuffs and process of making same



Patented Feb. 23, 1932 UNITED STATES PATENTOFTFICE MAX scniun), orRIEHEN, NEAR BASEL,'.AND rnrr'z s'rRAunoF IBAVSEL, swrrznnnnnn,

ASSIGNORS TO SOCIETY OF CHEMICAL INDUSTRY :IN B AS LE, E BASEL, SWITZERLAND No Drawing. Original application filed July 19, 1928, Serial No.294,044, Patent-no. 1,791,432,1lated AZODYESTUFFS AND PROCESS OF MAKINGS AME February 3, 1931, and in Switzerland July 26, 1927. Divided andthis applicatioufiled August 26,

1929. Serial No. 388,613.

This application is a division of application Serial No. 294,044, filedJuly 19, 1928.

This invention relates to the manufacture of new dyestuffs by couplingan aromatic unsulfon ated diazo-compound of the general formula RN=NRN=Nwherein the Rs stand for aromatic nuclei of the benzene series, withpyrazolone derivatives of the general formula diazo-compound of thegeneral formula RN=NR wherein the Rs stand for aromatic nuclei of thebenzene series. The

are insoluble in water, but soluble in various organic solvents withyellow to orange, red

or brown colorations.

Among these compounds those are particularly valuable which derive frompara-aminoazo-dyestuifs. v

The following example illustrates the invention the parts being byweight Emample usual diazotized. The filtered diaz o-solution is pouredinto a solution' alkaline withsodium carbonate or acid with acetic acidwherein R means an aromatic unsulfonated products are orange to brownpowders which 19.7 parts of amino-azo-benzene are as of 15.6 parts of5-pyrazolone-3-carboxylic acid ethyl ester. The dyestuff thus obtainedis isolatedby suction. 'Dried it forms an orange-yellow powder,dissolving in'alcohol with an orange coloration, which may be employedfor the dyeing of cellulose varnishes, such as Zapon varnishes, and thelike. These materialsare dyed in clearor'a nge tintsvery fast to light.The formulaiofthisi dyestu'fi' dyestufi's, such for; example asamino-a20- toluene, or the coupling products from diazotized aniline andoz-naphthylamine, diazotized.

p-chloraniline and meta amino-para-cresol ether, and the like5 there areobtained with the 5 -pyrazolone-3- carboXylic acid ethyl ester varnisheshaving orange "to brown tints. Similar products are 7 obtained .with themethyl or propyl ester of the pyrazolone. What we claim is h 1. Themanufacture of azo-dy'estufis by coupling 'pyrazolones of the generalformula with an aromatic unsulfonated diazo-c'om- NRN= N wherein the Rsaromatic nuclei of the benzene series.

1 2. The manufacture of azoedyestufi's by coupling the pyrazolone of theformula with diazotized amino-azo-benzene of the formula 'N nN O 7 poundof the general 1. formula B ll-* stand for fif; r r "1,847,025

7 3. As new products the azo-dyestufl's corresponding with the generalformula COO=a1kyl v h r V 1 in WhichR meansanaromaticunsulfonated.

.diazo-compound of the general formula V, R-N=N.R wherein the Rs standfor aromatic nuclei ofthe benzene series, which 7 I products form orangetodark brown powders whichdissolve in variousorganicsolventswithorange,ired or browncoloration; {5 4. As a new product theazody estuff corresponding with the formula H ({i-CObCzHs V 'YYN.

which product forms an. or nge; powder V which is insoluble in water butsoluble in various organic solvents to solutions of oraiige coloration.i i

,In witness whereof we have hereunto signed our namesthis. 514th dayofAugust,

MAX SCHMID. "FRITZ STRAUB;

